Winner Winner!!!!

[Dire_Moonfang]

Adam Taylor age 18

I was a nerd all throughout school always getting straight A's at times having to help the jocks pass or I would end up with getting a swirly at the closest toilet as I graduated.
I worked part-time at a local game store barely getting paid much when I heard the lotto was now at seven hundred million I decided why the hell not and bought a ticket knowing the chances of me winning were not in my favor but as luck turned out that night they announced the numbers and I had all eight I was ecstatic over the next week I meet with the lottery association as I was presented with a big check.

My life changed overnight the people that knew me in school started to come out of the woodwork calling me up or showing up at my parents house unannounced I didn't know what I would do with my winnings so the first thing I did was pay off my parents mortgage as well buying me a small house on about a small acre over the following months I kept getting calls but one day I got a call from someone I knew growing up as I listened to her telling me she wanted to meet up.

I couldn't help but smile thinking maybe my life was turning out great after all as we talked back and forth I finally said: "Hey you want to grab lunch with me." As I listened to her response not really knowing what she was really after. As I got dressed and drove to the nearby restaurant as I was seat at a nearby table I couldn't help but catch glances of nearby people whispering and pointing in hushed tones.

 

[Opensesame54321]

Caterina Classen sucked hard on the cock in her mouth, looking up at the man that she knelt in front of. His fingers gripped her long red hair and the groan that he made told her that he was about to cum. She starting pumping with her hand, alternating it with sucking and licking it.

"Mmmmmm! So good. You're so hot." She would have called him by name but, damn, it had slipped her memory. It didn't matter, as the next instant he thrusted into her mouth and she was busy sucking and swallowing his seed.

Finally he finished and she licked his cock clean before standing. The man stood there, his cock spent and peeking out of his jeans.

"You sure that you're 18?"

She grinned at him. "Yep."

"Well, you can fill your tank. I'll turn on the first one. If you ever need more gas, just ask for Justine."

She walked out from the back room and went outside to the pumps. Sure enough, he had flipped the pump on and she quickly filled up her car's tank.

In the car, she looked at the newspaper article about Adam Taylor winning all that lovely money. For that much money, she'd let him do anything to her. She really had wanted nothing to do with the goofball. But now...

He had sounded interested when She call. And he would be interested when he saw her at the restaurant. She was determined to help him spend some of that $700,000,000.

She found him easily enough in the restaurant. He somehow didn't seem to fit in here. She walked over to him, knowing that her short tight skirt would get his attention.

"Well, hello Mr. Lucky!"

 

[Dire_Moonfang]

I couldn't help but stare as I watched Caterina walk into the restaurant I couldn't help but make a gulp sound here and there as she came up and said those words I still couldn't believe my luck "Wish I was this lucky in high school."

I couldn't help but smile widely still staring at her outfit choice "I haven't seen you since graduation what you been up to?" I could feel myself get a hard on just from being across from her as the waitress came over and showed us each the menu.

As I picked out the biggest thing on the menu a twenty oz steak with all the fixings and for a drink a white wine bottle as I looked to Caterina giving her order I couldn't help but feel drawn to her like I was back in high school still willing to follow her as a love struck puppy.

 

[Opensesame54321]

I haven't seen you since graduation what you been up to?

"Oh, not much. I've really been bored lately. Nothing at all to do."

She smiled her most radiant smile at him and tried not to laugh as he ordered while wine with his steak. She ordered Dayboat scallops with Jasmine rice and fresh green beans. This was much tastier than the Big Mac and fries she was going to have to eat. Maybe if she played her cards right, she could avoid fast food all together.

While they ate, she tried running her foot up his leg. Occasionally she would pretend that it was an accident.

"Oh Adam, I'm so sorry. I didn't mean to." Her top was low cut and showing plenty of cleavage.

 

[Dire_Moonfang]

I smiled listening to Caterina talking as the food came and we began to eat I felt her leg touch mine as she said apologized I couldn't help but make a coughing sound as I said: "It's quite alright the table is a bit small isn't it." As I said that I couldn't help but look down at her low cut as I stared intently at her chest catching a full glimpse of you beautiful breasts.

"I was thinking of doing a bit shopping after this before I went home would you be interested in humoring me a little longer if there is anything you need I wouldn't mind buying it for you."

My mind was going forward with ideas on where to take her the clothing store would be the first stop getting her whatever she wanted I was loving the attention I was getting from her and I couldn't wait to shower her with anything her heart wanted.

As I finished my meal I popped open the cork opening the wine that came with my steak as I looked to Caterina and said "Would you care for a drink before we go I know one glass won't hurt."

 

[Opensesame54321]

Shopping! She felt warm all over just at the thought of spending his money. Wonder what she could convince him to buy for her? Clothes? Furs? Undies?

"Oh, you don't have to buy me anything, Adam. But I would love to spend the afternoon with you." She gave him her best smile and leaned forward, showing him a bit more cleavage.

He popped the cork in the wine bottle and offered her a glass.

"Oh, Adam, I'd love a glass!" She wrinkled her nose with a smile as she held out her glass and ran her foot up his leg. "Oh, sorry."

 

[Dire_Moonfang]

I smiled as wide as I could as Caterina agreed to go shopping with me I then felt her leg rub against mine once again as I heard her say "Oh Sorry." I couldn't help but gulp and say "it's my fault really."

As we sat there for a bit more drinking the alcohol right across from my crush from high school as we finished our first drinks the check came as I placed down an even hundred giving the waitress a much-deserved tip as we walked out of the restaurant.

I looked to Caterina and said, "If you want you can ride with me show me which stores are a must." I clicked the button on my key ring making the horn sound from my car. I couldn't take my eyes of her body it was made for a goddess I couldn't help but think what I would do to her body tasting every inch of it with my tongue.

 

[Opensesame54321]

She smiled as she watched him drop a $100 as if it was nothing. No more giving blow jobs to pump jockeys just for a tank of gas. And if she was lucky, she could string Adam along, get plenty of stuff from him and never have to put out. The guy was naive - probably a virgin, probably never even seen any pussy except in a magazine or in a porno flick. Certainly not in the flesh. And if she had her way, see it would be as close as he would get to her pussy, if that at all.

As they left, she slipped her arm through his and pressed her boobs against his upper arm.

If you want you can ride with me show me which stores are a must.

"Ohhhh, Adam, I'd love to ride with you." She was anxious to see what kind of car he had bought with all his lovely money.

 

[Dire_Moonfang]

I smiled as I felt her arm underneath mine I couldn't help but feel the warmth from her breast I couldn't help but smile as I got what she was truly wanting to say I could imagine what types of things I could do to her "This is it I know she isn't much but she was my first buy with my first paycheck at work."

I opened the door to the truck as I looked to Caterina I thought I caught a look of disgust as I helped her into the truck I walked over to the driver side and gotten in as I started the truck I began to drive out of the parking lot and looked over and said "So what's the first stop I was thinking a clothing store but which one would be the best."

 

[Opensesame54321]

A truck! He bought a truck? It would not do for her to arrive in this thing, even if it was new. She would have to work on him.

Smiling at him, she said, "Wow. The first thing that you purchased? I would have expected to see someone sexy like you in a Porsche or a Ferrari. Something that would let the world know what a hot stud you are."

She looked out the window, wondering where they were heading.

"So, Adam, where are we heading to first? I'm sure that you have lots of things that you want to get. We can get you some nice clothes"

She smiled at him as she sat in the passenger side of the truck, making sure that the way she sat let her skirt ride up high on her thighs.

 

[Dire_Moonfang]

I smiled as I began to drive towards the nearby mall "Why settle for one clothing store. As I drove I couldn't help but take a glance at her body here and there in the back of my mind I was thinking of all the lewd stuff me and her could do I laughed as I thought she probably thinks I am still a virgin.

I was lucky to lose my virginity but it was to one of the chess club girls's in school as I turned the corner driving into the mall parking lot I looked over to Caterina as I said "We are here." As I got out of the car I walked over to her side as I placed my hand wanting to help her out of the truck.

 

[Opensesame54321]

Caterina watched him park and get out of the vehicle. In her head, she was figuring just how much she could get from him without even having to put out. If she played this little virgin right, maybe she could get a new wardrobe, even a new car. Or a vacation to some exotic place like Paris, or the Rivera or something like that. He had lots of money now. He wouldn't miss a couple of hundred thou. She just needed to play him right.

He opened the door to the truck and offered her his hand. She took it and slid down, pretending to lose her balance and fall into his arms. Her skirt seemed to snag on the truck seat, sliding the skirt up and flashing her panties. She pretended to be embarrassed, apologizing profusely to him.

"Oh Adam, I'm so sorry. Clumsy me. Please forgive me." She stayed in his arms a moment longer than necessary before straightening her clothes and pulling herself together.

Maybe she could even get herself a new apartment, rent paid of course.

 

[Dire_Moonfang]

I couldn't help but stare as she got out of the truck as I caught a glimpse of her panties I tried to look away but they were right in my view as my hand wanted so hard to touch them feeling her sex with my hand I finally got up the courage as I said "It's alright Caterina no harm done." But in the back of my mind, I was thinking of every naughty thing I could do to her. As we went inside the mall to the first clothing store there it turned out being a woman's store as I became wide eyed as I turned to Caterina and said "Sorry I got turned around but since we are here why not take a look and see if you like any outfits."

 

[Opensesame54321]

Stepping into mall, he pointed out a women's clothing store, suggesting that she might find something that she would like. She could feel her heart beating faster. She knew that she could find plenty to fit her and even more. They slowly walked into the clothing store.

"Oh, Adam, we came here for you, not for me." She tried to look demure, though she saw many outfits that she practically drooled over. With a passionate longing, she wistfully felt the silky kimono hanging on the nearby rack. She knew that it would look hot on her.

Yes, if she played her cards right, she could really get some nice things from this dork. Correction, rich dork.

 

[Dire_Moonfang]

I chuckled as I listened to Caterina say "Oh, Adam, we came here for you, not for me." My face became a bit red as I said "To be honest the real reason we came to the mall wasn't for me to clothes shop it was more to see you try on the clothes because let's be honest I find you so fucking hot and I would give anything just to see your body what do you say? As I said that last thing I couldn't take any of it back at this moment I didn't really want to I looked around to make sure no one else heard what I said I turned back to Caterina waiting for her to either smack me or scream at me and call me a pervert.

 

[Opensesame54321]

To be honest the real reason we came to the mall wasn't for me to clothes shop it was more to see you try on the clothes because let's be honest I find you so fucking hot and I would give anything just to see your body what do you say?

She looked away feigning embarrassment, but really she was thinking to herself, 'Why that little devil. I may have to stay on my toes.'

She gathered herself together before turning back to face Adam. She gave him a shy smile and actually fluttered her eyelashes at him. "Why, Adam, I had no idea that you felt that way about me. I'm very touched. Is there anything in particular that you would like to see me in?"

 

[Dire_Moonfang]

I was actually happy when Caterina didn't do anything except smile that smile I couldn't help myself as I said: "I was thinking of seeing you in that silky kimono you touched I know it would look hot on you." As I said that I looked around the store seeing a few girls hearing my comment I began to blush as I remembered I was in a woman clothing store as I said all this stuff as I watched her go back to the outfit and take it off the rack I couldn't help myself as I followed her toward the dressing room watching her ass sway back and forth I couldn't help myself as I said "Fuck." I looked around as I could hear girls around the store start to chuckle.

 

[Opensesame54321]

Oh, this was gonna be a piece of cake. She had wanted that kimono and she was pretty sure that he would get it for her. Picking out her size, she walked towards the dressing rooms, hearing him behind her, panting like a little puppy. Some of the other girls were looking at him, recognizing him from his picture in the paper.

She was afraid that if she left him waiting for her outside the dressing room that one of them would try to snap him up. This was her meal ticket and she did not share.

"Now, if you promise not to peek, I'll let you come in the dressing room with me. But you must turn your back to me and face the wall. And no peeking!" She pulled him into the dressing room with her and turned him to face the wall.

 

[Dire_Moonfang]

I couldn't help but smile as I was allowed inside the dressing room with her as I followed her inside I felt Caterina turn me around at the wall not daring to catch a peek I was tempted as I heard Caterina clothes dropping to the floor I couldn't help myself but say "You know this not fair at all what you're doing keeping me in this room when I can't even glance at you." As I heard a small chuckle I couldn't help myself groaning at not being able to look at this gorgeous beautiful creature naked body I could just imagine how her tight breasts looked with my tongue on each mound as this was happening I didn't realize that I was sporting a hard-on through my loose boxers and my baggy pants.

 

[Opensesame54321]

You know this not fair at all what you're doing keeping me in this room when I can't even glance at you.

She gave a little giggle. "Why, Adam! You are such a naughty boy!" She giggled again, loving all the power that she had over this naive kid.

"You can turn around and let me know what you think!" She had the top on and did a little pirouette for him.

"What do you think? Do you like it?"

 

[Dire_Moonfang]

As I turned around and took a plentiful view of Caterina in that sexy kimono my mouth was agape as I began to stutter "You look absolutely stunning there are no words to describe how you look at this moment." I couldn't help myself as I took a few steps towards her not knowing what I was going to do "I don't mind buying that for you." As I said that I couldn't help but blush feeling a slight rush of blood going to the one place I wasn't expecting at this moment as I looked down seeing the tent in my pants as I looked back up to Caterina face trying to figure out her reaction.

 

[Opensesame54321]

He turned around and his reaction was a pleasure to behold. His mouth fell open as he stared at her and she noted that his cock was pointing straight at her.

She looked shyly at him. "Why Adam, I do believe that you find me attractive." She acted shy though she did wonder just what his cock tasted like. She wondered what it was like to be fucked by him. The poor thing probably wouldn't know what to do.

And she wondered what else she could get out of him.

"Oh, naughty! Now turn around so I can change." She accidentally let her hand brush against the front of his pants. "Sorry Adam. Now be good and turn around so I can change clothes."

 

[Dire_Moonfang]

I couldn't believe how my luck was changing for the better with each passing moment as I shook my head up and down and said "Ok." As I turned around trying not to turn around I looked down at my hard on still forming the tent in my pants as I said: "That's just it Caterina I find you the hottest thing in this world hotter than any supermodel or porn actress combined." I waited there for god knows how long wondering what her reaction would be to my statement I couldn't stop thinking of all the ways I would give her pleasure but as I thought about that a few wonderful ideas began to form in my head maybe I could get at least a pity handjob from all that I bought her today.

 

[Opensesame54321]

Wow! He was really crazy for her. She had it made! The words sang over and over in her head. Once he had turned away, she went up and hugged his back.

"Oh, Adam, you are such a gentleman!" Her breast were pressed against his back. "Now, you be good and I'll finish getting dressed. Okay, sweetie?" She gave him a squeeze and finished dressing.

 

[Dire_Moonfang]

I was taken back as I felt Caterina breasts against my back as I dreaded hearing those words "Be good." I didn't want to be good I wanted her body so bad I was tempted to take a peek but not knowing what she would say I stood there not moving as my cock stood there rock hard in my pants this wasn't fair making me stand here like this but I was willing to go with whatever to have a chance at Caterina she was a goddess in my eyes.

As I waited there for about a good five minutes before hearing Caterina's voice speak to me saying she was done changing I turned around as I saw her in the outfit she wore into the store as I gulped I looked down at my tent saying "I think you should go out first that way no one see's this." I said pointing down to my cock.